Methyl acetoacetate → 4-Pentenoic acid, 2-acetyl-, methyl ester

Participants

Reaction Steps

A mixture of methyl acetoacetate (11.6 g, 100 mmol), allyl bromide (12.1 g, 100 mmol) and potassium carbonate (13.8 g, 100 mmol) in acetone (70 mL) is heated under reflux for 18 hours. The mixture is filtered and the filtrate is evaporated. The residue is chromatographed on silica gel (15:1 hexane:ethyl acetate) to give methyl 3-oxo-2-(1-propen-3-yl)butanoate (8.8 g, 47%): 1H-NMR (300 MHz, CDCl3) δ (TMS) 2.22 (s, 3H), 2.58 (t, 2H), 3.54 (t, 1H), 3.72 (s, 3H), 4.90-5.12(m, 2H), 5.60-5.82 (m, 1H).

Provenance & Evidence